Chirality plays a central role in organic and bioorganic chemistry. Hence the synthesis of optically-active compound is an important endeavor. We have found certain B-alkyl-9-borabicyclo(3.3.1)nonanes(9-BBN) reduce aldehydes and alkynyl ketones under remarkably mild conditions. The reagent derived from alpha-pinene and 9BBN induces a high degree of optical activity into the alcohol product. For example benzaldehyde-alpha-d and 4-methyl-1-pentyne-3-one are reduced to the corresponding alcohols with essentially complete asymmetric induction. Mechanistic investigations have shown that these reactions proceed via a six-centered cyclic process rather than a dehydroboration-reduction process. For other ketones, such as acetophenone, the dehydroboration-reduction process becomes important. It is anticipated that control of reaction pathway will lead to high asymmetric reductions with ketones. The chemoselectivity of the reagent will be investigated. It is anticipated that many functional groups, such as the cyano, ester, epoxide and nitro groups, will be inert to the reagent. Other functionalities such as cyanoketones, alpha-ketoesters, and imines may be reduced. These should provide access to optically-active cyanohydrins, alpha-hydroxy acids, beta-hydroxy amines and amino acids. The use of optically-active propargyl alcohols for the synthesis of lactones and butenolides and other natural products will be explored. These studies should provide easy access to a wide variety of optically-active substances which are of interest in biochemical and pharmaceutical research.